Whether it's for a podcast or a live event, knowing how to host a successful "fireside chat" will make all the difference between delighting your listeners and losing them.

To find out the top keys to a brilliant interview, I asked the best interviewer I could think of, Guy Raz, who is the host, co-creator, and editorial director of three NPR programs, including two of its most popular ones: TED Radio Hour and How I Built This (heard by more than 14 million people each month). Raz has interviewed more than 6,000 people, including Mark Zuckerberg, Bill Gates, and Eminem.

How I Built This, one of the top-20 most downloaded podcasts in the United States in 2017, dives deep into the stories of some of the world's most successful entrepreneurs, including CEOs like Herb Kelleher, the founder of Southwest Airlines, Jim Koch, the originator of Samuel Adams, Sara Blakely, the creator and CEO of Spanx, and many others. So far, the show has published 84 episodes, many of which feature a personal behind-the-scenes look into the lives of successful billionaires.

Below, Raz shares openly about how to find great guests, how to create trust and go beyond surface-level answers, why failure is his favorite topic, and how he first found his voice.

Guy Raz's 7 Takeaways on How to Tell the Stories of Icons and Billionaires 

1. Great interviews start with a "generous" guest.

"There are lots of very successful people in the United States and around the world, but we're really looking for people who can offer their generosity," said Raz. "And what I mean by that word is their generosity of spirit, their willingness to look at their failures, their setbacks, and to show vulnerability. If you have the ability to do those things, we're pretty confident we can pull a story out of you."

2. Create a safe place for your guest to do a "trust fall."

"In those cases [when a guest is hesitant], I really try to break the fourth wall and say, hey, our listeners will like you more, will identify with you more, and I promise will want to communicate with you and be moved by what you say if you can try and reach into your mind, soul, whatever, your past. And open up. And do kind of a trust fall," said Raz.

This secret to asking a potentially embarrassing question--like the one he asked Square's VP of Global Sales on a live stage at Dreamforce 2017, "What was one of the most humiliating sales calls you ever did?"--is how Guy Raz has built a reputation for being able to unearth details other hosts might shy away from. 

"You know the trust fall side of it is hard," Raz said. "But I've been doing this for 20 years and many of the people I interview have been listening to me for a while so I'm lucky in that a lot of them know and can trust that I will treat their story with respect, fairness, and sensitivity."

3. A really good question comes from getting swept up in the story and embodying your guest.

It's common knowledge that open-ended questions are better for starting conversations than closed-ended questions, but Raz frequently asks binary questions, such as the questions he asked Kevin Systrom and Mike Krieger, the co-founders of Instagram: "Were there moments, especially in the beginning, where you thought this could fail?" Or "So, very shortly after you launched this thing it's valued at, like, more than $20 million or something, right?"

His questions may seem limited, as in, a yes or no would answer the question, but what's really happening under the surface is Raz has embedded a bigger story in a seemingly simple question and it requires the guest(s) to unwrap the layers.

In other words, Raz leverages the entrepreneur's compulsive need to fix problems by presenting them with a problem--in the form of a question--to solve. 

"It's less methodical and thought out [than you think]," he told me. "Look, all I do is I get swept up with the story. It's like going to see a horror movie and being like, AHH! Don't turn that corner, don't go in the kitchen. Because I'm in the moment with them and I'm asking them to take me on a journey and I'll guide them a little bit."

Researching your guest beforehand is the key to guiding and shaping the story. Raz frequently tees up an interesting anecdote--without giving it away--for his guests to knock out of the park.

"I'm good at guiding them but I also want to be surprised," he said. "And even when I kind of know the story I still find myself feeling surprised to hear them describe it in their own words. So it's really about me kind of embodying them while they're telling the story and trying to imagine what it felt like and that's really where my reactions come from. Like, oh my god, that happened?! That person--you saw them again in the bar with your new wife, that must have been terrifying!"

This genuine empathetic curiosity is what Raz is known for, and it often leads to powerful moments on the show, such as the time when media mogul Troy Carter broke down talking about how one of his deepest motivations in life was to make his mother proud.

4. Get past a canned answer by asking your question in a different way, and don't be afraid to be persistent.

If you regularly interview high-profile executives, at some point you'll receive a bland, vanilla answer, or a guarded one from your guest. When this happens, Raz circumvents the canned answer to get a deeper insight, by re-phrasing the question and not giving up.

"I'm sort of a--you can call it a master or an annoyance," said Raz. "I'm very persistent. I often say to people, I know you've been asked this question but I'm asking it in a slightly different way because I think there's a different answer here. I'm very straightforward with people. I'm not trying to trick them. I think that most people have pretty good stories to tell but I think a lot of people are cautious and want to protect themselves and that's natural." 

When inquiring about someone's biggest life failures, it can be an intimidating thing to ask, especially if it's going to be broadcasted to millions of people.

"I'm asking somebody to open themselves up in a way that they probably wouldn't to anyone except maybe their priest or their therapist," said Raz. "It's a big deal. And there are times when I interview somebody and they do reveal a lot and it is powerful and then they'll call me later and say you know I have second thoughts about this. I don't know if I've told too much."

When this happens, it takes a delicate reassurance that vulnerability is worth it. And, so far, according to Raz, it always has been.

"What I'll usually say is look let me finish editing this, let me finish putting it together and take a listen. And I'll give you my honest feedback. Every single case where that's happened, where I've convinced the person to just trust us, it's been amazing. People have come out and said thank you for sharing your story of depression, thank you for sharing your story of vulnerability or failure, like, that has changed me, that has made me a stronger business person or stronger person. It's been amazing. And there are many examples with How I Built This where that's happened."

5. Don't over-script the conversation, instead, guide the flow. And edit later (if it's a podcast).

What listeners actually hear on How I Built This is only a third of the full conversation. It's usually a two-hour interview that gets cut down to about 45 minutes.

You might not have a robust production studio like NPR, but as you edit, keep in mind that the end result his team shoots for is a great narrative with interesting lessons learned along the way.

This clean narrative isn't always easy to facilitate. Even with the smoothest of hosts, the conversation can get off track or a guest can lose their train of thought. And sometimes the mic needs to be turned off.

"I'll try to wind back to something that we explored but hadn't fully explored. I'll stop the interview and say, hey, you know, I'm feeling like we're kind of going in different directions. Let me try to explain where I'm trying to go and see if we can go in that direction because I promise you in the end what will come out of it will be something really unique and different."

When it comes to structuring a talk, the storyteller said there are no rules and he tries a bunch of things, with lots of improvising, especially if he's interviewing someone live on-stage. Well-researched notes are the key. Raz refers to his notepad as a "dynamic document."

"I constantly shift around topics and questions in the back of my mind throughout the interview," he told me.

6. His favorite topic to bring up isn't success. It's failure, because he's seen firsthand in his own life the power of overcoming challenges.

If you've ever listened to an episode of How I Built This, recall how it starts out with an excerpt of the guest describing a crushing, hopeless moment in his or her life. It's a jarring depiction of situations where the founder ran out of money, ruined a dear relationship, or watched their company's stock plummet in value. By starting out with a dire "rock bottom", Raz creates a curiosity gap that immediately hooks the reader.

"Failure is really, really interesting," said Raz. "I think it also gives hope to people who may not yet have achieved the kind of success they're hoping to achieve."

"I'm really interested in vulnerability. I'm interested in crisis."

Raz is no stranger to crisis in his own life and shared about the struggles he's faced.

"I, myself, when I was a younger man, dealt with really severe depression," he said. "I was very embarrassed about that depression in my early and mid-twenties. And I secretly went and saw help and went on medication. Now I'm very open about it because I want younger people who think of me as a successful radio and podcast creator to feel like it's okay--that in your life you will have moments of difficulty, and vulnerability and sadness and other things--but that they may very well pass and you could very well get to the places you want to get to. So I'm always looking for those moments of vulnerability, humanity, or challenge. Those are the kinds of stories I'm always really trying to find."

7. Screw journalism codes. Use your own voice.

"There's no roadmap," he said, to find your unique voice. For him, there was a point in his career when he realized he didn't have to be like other radio personalities.

"When I started out at NPR twenty years ago, I thought I had to sound like other NPR men to be a radio personality or host. And I did that for the first two years. But over time, I found my own voice and my own approach for who I am. It was almost like I had to be something else to be who I am in order to get back to who I actually am."

That breakthrough moment came from one of his first interviews as a host with a woman named Ingrid Betancourt, who was a prisoner of the Colombian paramilitary group the FARC for seven years in the jungles of Colombia. She was eventually released, wrote a book about it, and when she came in for an interview, it was more powerful than he expected. 

"I was very, very affected by it--emotionally moved by it," Raz remembered. "It was really the first time where I realized I didn't have to pretend I wasn't moved by it. I didn't have to pretend like this didn't make me sad. Because it was. And that was a moment where I thought, you know what, screw all these journalism codes and rules about objectivity. They're nonsense. We're not robots. We're human. And we should act and respond like humans to other human beings."

Published on: Apr 4, 2018